In a silver halide photographic element, a color image is formed when the material is exposed to light and then developed using a primary amine color developer. The development results in imagewise reduction of silver halide and the corresponding production of oxidized developer. The oxidized developer then reacts in an imagewise fashion with one or more incorporated dye-forming couplers to form a dye image.
Magenta dye-forming couplers are employed in subtractive color forming processes. One of the principal coupler types useful for this purpose are those based on a pyrazolone ring. Pyrazolone-based couplers having a coupling-off group linked to the pyrazolone ring by oxygen have long been considered as potentially attractive two equivalent magenta couplers. An oxygen-linked coupling-off group could impart increased activity to the pyrazolone coupler; however the general instability of these couplers toward ambient oxygen makes them difficult to synthesize and impractical for use in a film environment since they decompose during keeping. In particular, pyrazolone couplers having an anilino or acylamino substituent at the 3-position have exhibited unacceptable stability when an aryloxy is employed as a coupling-off group. As a result, pyrazolone couplers have employed either so-called "four equivalent" couplers containing hydrogen at the coupling-off position or have employed so-called "two-equivalent" couplers containing a coupling-off group having a sulfur or nitrogen atom linked to the pyrazolone ring.
U.S. Pat. No. 3,419,391 discloses certain types of pyrazolone-based compounds as two-equivalent couplers having high dye-forming reactivity and reduced tendency to form color fog. According to the patent, the pyrazolone ring is not limited to the presence of any particular substituents at the 3-position or elsewhere. Specifically identified substituents at the 3-position include anilino, acylamino, alkyl, amino, alkoxy, amido, carbamoyl, ureido, thio, guanidino, etc. The couplers of the patent may contain an aryl group at the 1-position and, among other things, an alkyl or carboxy ester group at the 3-position. The aryloxy couplers of the patent are said not to produce color fog (printout) and to provide improved reactivity. Thus, they are said to provide low printout or yellowing in Dmin areas when they are exposed to light or high temperatures, respectively, subsequent to development. No mention is made of the poor keeping of pyrazolone couplers having aryloxy coupling-off groups although their instability is well known in the art.
U.S. Pat. No. 5,576,167 describes a family of two-equivalent pyrazolone couplers with good stability towards oxygen. The features that make these compounds stable are: (a) an electron-withdrawing CXYZ substituent in the 3-position of the pyrazolone ring, and (b) an aryloxy group, further substituted by electron-withdrawing group(s) in the 4-position of the ring. Although stable, the couplers of this patent require a multistep procedure for their preparation and some of these steps are difficult to perform. None of these references discloses magenta couplers of this invention.
In a co-pending application we describe 1-aryl-3-arylpyrazolo-5-one magenta dye forming couplers that are stable during synthesis, film manufacture, and during film keeping and are not difficult to prepare. However, in general, these couplers are not crystalline and therefore difficult to manufacture.
It would be desirable to have magenta dye forming couplers of the 1-aryl-3-arylpyrazolo-5-one and/or the 1-aryl-3-alkylpyrazolo-5-one type that are stable during synthesis, film manufacture, and during film keeping that would provide acceptable hue and reactivity but which would be crystalline.